A certain class of natural products is formed in nature first by action of ADH-like enzymes on a starting material, followed by spontaneous (non-enzyme-catalyzed) steps that generate the final structure. One such product, Compound P, was formed when the ADH-like enzyme was provided with NAD²H₂ as cofactor. (As a reminder, NAD²H₂ is NADH wherein both transferable hydrogens have been replaced by deuterium.) 1. ADH-like enzyme, NAD²H₂ ° 2. spontaneous steps Starting Material I I OH Compound P Using NAD²H₂ as cofactor, provide a complete curved-arrow mechanism for this transformation. Make sure your mechanism accounts for the location of the deuterium in the product. For the spontaneous steps, you may use general acids and bases, but no other cofactors. (Hint: numbering your carbons will be helpful.)
A certain class of natural products is formed in nature first by action of ADH-like enzymes on a starting material, followed by spontaneous (non-enzyme-catalyzed) steps that generate the final structure. One such product, Compound P, was formed when the ADH-like enzyme was provided with NAD²H₂ as cofactor. (As a reminder, NAD²H₂ is NADH wherein both transferable hydrogens have been replaced by deuterium.) 1. ADH-like enzyme, NAD²H₂ ° 2. spontaneous steps Starting Material I I OH Compound P Using NAD²H₂ as cofactor, provide a complete curved-arrow mechanism for this transformation. Make sure your mechanism accounts for the location of the deuterium in the product. For the spontaneous steps, you may use general acids and bases, but no other cofactors. (Hint: numbering your carbons will be helpful.)
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter27: Amino Acids And Proteins
Section: Chapter Questions
Problem 27.50P
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![A certain class of natural products is formed in nature first by action of ADH-like enzymes on a
starting material, followed by spontaneous (non-enzyme-catalyzed) steps that generate the final structure.
One such product, Compound P, was formed when the ADH-like enzyme was provided with NAD²H₂ as
cofactor. (As a reminder, NAD²H₂ is NADH wherein both transferable hydrogens have been replaced by
deuterium.)
1. ADH-like enzyme, NAD²H₂
°
2. spontaneous steps
Starting Material
I
I
OH
Compound P
Using NAD²H₂ as cofactor, provide a complete curved-arrow mechanism for this transformation. Make sure
your mechanism accounts for the location of the deuterium in the product. For the spontaneous steps, you
may use general acids and bases, but no other cofactors. (Hint: numbering your carbons will be helpful.)](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F48fe4e77-f9ef-48e7-bc1d-608abf2bf6f8%2F46f3ca7d-028f-41cb-a17d-b48f009409ce%2F9zi0z18_processed.png&w=3840&q=75)
Transcribed Image Text:A certain class of natural products is formed in nature first by action of ADH-like enzymes on a
starting material, followed by spontaneous (non-enzyme-catalyzed) steps that generate the final structure.
One such product, Compound P, was formed when the ADH-like enzyme was provided with NAD²H₂ as
cofactor. (As a reminder, NAD²H₂ is NADH wherein both transferable hydrogens have been replaced by
deuterium.)
1. ADH-like enzyme, NAD²H₂
°
2. spontaneous steps
Starting Material
I
I
OH
Compound P
Using NAD²H₂ as cofactor, provide a complete curved-arrow mechanism for this transformation. Make sure
your mechanism accounts for the location of the deuterium in the product. For the spontaneous steps, you
may use general acids and bases, but no other cofactors. (Hint: numbering your carbons will be helpful.)
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